Buying Online Businesses Podcast

This episode is an eye-opening case study where Jaryd Krause sits down with AJ, a Buying Online Businesses graduate who made the leap from running a large IT team at a global bank to building an online business portfolio. AJ shares how he went from launching a failing startup to successfully acquiring a $50,000 media and membership business that now generates $2,000 net profit per month—all within just six months. Inside this conversation, you’ll know: ✔️ Why AJ abandoned the startup path in favor of buying an existing business✔️ The exact business model he chose—and why it stood out among the rest✔️ How he saved money on the acquisition price (including what multiple he actually paid)✔️ The due diligence steps he took to minimize risk before signing the deal✔️ The hardest part of buying a business (his answer may surprise you)✔️ His best advice for first-time buyers—and what’s next as he builds his portfolio Packed with lessons from someone who’s navigated the challenges and emerged profitable, this episode is a must-listen whether you’re planning your first business acquisition or aiming to master your due diligence process 🎧 Tune in to learn how AJ turned a $50K deal into a reliable income stream—and how you can apply the same strategies to your own acquisition journey.   Episode Highlights 09:47 – Llearning how to properly evaluate businesses instead of jumping straight into a deal. 13:38 – Defining non-negotiables: valuing time, lifestyle, and family more than owning a “sweet deal.” 18:22 – How looking at hundreds of businesses sharpened AJ’s ability to spot red flags and opportunities. 21:14 – There are no unicorns—every business has cons; it’s about choosing what risks you can manage. 26:55 – Why the decision to “pull the trigger” is the hardest part of the acquisition journey. 35:52 – Advice for first-time buyers: don’t skip the learning stage—education reduces fear and regret. 41:55 – The difference between being a business operator and becoming a true owner with leverage. Key Takeaways ➥ There’s no such thing as a perfect business. Every deal has risks; the key is knowing which ones you can live with and mitigate. ➥ Start with education. Skipping the learning phase leads to regret; preparation makes the acquisition less scary and more strategic. ➥ Taking the leap is the hardest part. Eventually you must stop analyzing and trust your due diligence to move forward. ➥ Aim to work on the business, not in it. Leveraging teams and managers turns you from operator into true owner. ➥ Bigger opportunities become realistic after the first acquisition. The initial win builds confidence to pursue larger, even debt-financed, deals. About AJ AJ is a BuyingOnlineBusinesses.com graduate who went from being a corporate employee running a large IT team for a global bank. To now an online business owner and building a portfolio of businesses.    Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this power-packed episode, Jaryd Krause sits down with serial founder and dealmaker Anthony Franco, a man who knows exits inside and out. Having built and sold seven companies—six of them successfully, including two to publicly listed firms—Anthony brings rare, battle-tested wisdom to the table. Together, they dig into what it really takes to engineer a successful exit in the $5M–$50M range. From preparing your business to maximize valuation, to structuring deals that minimize risk for both buyers and sellers, Anthony shares the strategies he’s used to navigate countless transactions. He doesn’t sugarcoat it either—every deal has “hair” on it, and this conversation unpacks exactly how to handle those messy, unexpected challenges that can tank a deal if you’re not prepared. You’ll learn:✔️ How to structure an exit so you walk away with more security and better terms✔️ Why taking your foot off the gas before closing can destroy your valuation✔️ How buyers can avoid catastrophic mistakes by spotting risk early✔️ What makes a business truly attractive to both strategic and financial buyers✔️ The evolving role of AI in business growth, exits, and even the future of work Whether you’re eyeing a future sale, planning to acquire, or just want to build a business that’s more valuable and resilient, this episode is a masterclass in deal-making straight from someone who’s been through it all. 🎧 Tune in now to hear how to prepare, structure, and execute smarter exits.   Episode Highlights 04:50 – Clean books, systems, and reduced key-person dependency: the essentials for any exit. 06:50 – Why every exit is messy—buyers always renegotiate during LOI. 08:30 – Sophisticated vs. inexperienced buyers: how the right questions signal experience. 09:35 – Knowing what really matters in due diligence vs. what’s just “wonky” small-business noise. 11:20 – Why trust and fairness between buyer and seller are critical when numbers vary near close. 12:50 – Sellers must keep operating like they won’t exit—taking the foot off the gas can kill deals. 18:00 – Why tax planning is just as important as negotiating the sale price. 25:40 – Selling fast matters—waiting too long risks copycat competitors and valuation drops. 27:40 – Regulation, trucking, and AI adoption: why safety perception, not data, drives adoption speed.   Key Takeaways ➥ Prepare early. Clean financials, diversified revenue streams, and reduced key-person dependency are critical to maximizing valuation. ➥ Buyers are risk-averse. Expect tough questions in due diligence—not personal attacks. Sophisticated buyers ask the right way, but all buyers are trying to mitigate risk. ➥ Deal structures matter. Cash is king for sellers. Earn-outs, seller notes, and rollover equity all come with risks—align them with your personal life stage and goals. ➥ Don’t take your foot off the gas. Deals can drag on for months. Keep running your business as though it won’t sell; growth during due diligence strengthens your negotiating power. ➥ Surround yourself with the right advisors. A good CPA and financial advisor can save millions in taxes and structure your exit properly. ➥ AI is changing the game. It will automate “crappy work,” commoditize parts of business, and put greater emphasis on distribution, brand, and audience trust. ➥ Faster is better. Once you decide to sell, speed matters—because markets and competitors don’t wait.   About Anthony Franco Anthony Franco is a seasoned founder, operator, and dealmaker who’s built and sold seven companies—six of them successfully, including two to publicly listed firms.  After working closely with the team at OneReach.ai, he realized traditional frameworks like Lean and Agile just don’t cut it in today’s fast-moving, AI-driven world. That insight led to the creation of the WISER Method—a new approach that helps founders build smarter, scale faster, and exit more strategically. He’s also a licensed business broker, and on his own podcast How to Founder, he shares real-world strategies for building businesses that are easier to operate and more valuable to sell. Connect with Anthony Franco ➥ https://www.linkedin.com/in/anthonyfranco/ ➥ https://www.aifirstprinciples.org/ Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this raw and eye-opening episode, Jaryd Krause chats with Matthew Tse—a former Big Tech software engineer who ditched the corporate grind to buy his way into freedom through online business. Today, he runs ImprovMX.com, a SaaS business he acquired after sifting through countless deals, failed startup attempts, and plenty of trial and error. Matthew doesn’t sugarcoat it. He shares the highs, the mistakes, and the exact process that helped him land the right acquisition to replace his income and build a life on his own terms. In this no-BS conversation, you’ll discover: ✔️ How many businesses do you really need to analyze before finding “the one”✔️ The critical mindset shifts that help you push through failed deals and land a winner✔️ Why chasing small, cheap businesses can actually cost you more in the long run✔️ The price range Matthew now recommends for friends looking to buy online✔️ His top growth levers for scaling SaaS—starting with retention before expansion If you’ve ever wondered how long it actually takes to buy an online business—or what it feels like to transition from employee to owner—this episode pulls back the curtain on the entire journey. 🎧 Tune in now and learn what it really takes to replace your income with a SaaS acquisition.   Episode Highlights 09:21 – Learning from others’ success can inspire acquiring an existing business instead of starting from scratch. 14:16  – Defining an ideal business model and price range narrows the search effectively. 17:11 – Focusing on businesses aligned with personal strengths leads to better outcomes than chasing every opportunity. 20:35 – Studying case studies and industry insights accelerates learning and reduces mistakes. 26:37 – Audience trust and built-in channels are more valuable than the product itself. 43:20 – Avoiding small deals and aligning acquisitions with lifestyle and skills improves success. 47:38 – Buying the right SaaS can replace traditional income while leveraging personal strengths effectively.   Key Takeaways ➥ Acquisitions can accelerate entrepreneurship—buying an existing business allows leveraging capital and skills to bypass the hardest startup challenges. ➥ Understanding your strengths and weaknesses is essential to narrowing search criteria and finding the right business model and price range. ➥ True value lies in the audience, reputation, and established distribution channels—not just the product or code. ➥ Preparation and research, including learning from others’ experiences and industry content, reduce risk and improve outcomes. ➥ Mindset, persistence, and patience are critical when evaluating hundreds of businesses to find the right fit. ➥ Post-acquisition growth is most effective when leveraging existing channels, retention strategies, and organic traffic. ➥ Being selective and strategic—rather than opportunistic—ensures acquisitions provide both ROI and lifestyle freedom.   About Matthew Tse Matthew Tse was a career software engineer in big tech & quant finance. He decided he wanted a more free & fulfilling life, and eventually stumbled his way into acquiring improvmx.com, which he's now running and growing.   Connect with Matthew Tse ➥https://www.linkedin.com/in/matthew-t-15565736/ ➥matthewtse.com ➥https://buyingonlinebusinesses.com/ep-212-how-to-start-buying-flipping-small-saas-businesses-with-andrew-pierno/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ GoDaddy (Website Hosting) - https://bit.ly/3YiRkWV ➥ Rank Math (WordPress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

In this sharp and savvy episode, host Jaryd Krause welcomes M&A heavyweight Michael Vann—President of the Vann Group and Principal at Eaton Square—for a deep dive into the brilliant… and brutally expensive mistakes entrepreneurs make when trying to grow through acquisition. With 25+ years of deal-making, scaling, and succession planning, Michael’s been in the trenches guiding businesses to multi-million dollar exits across industries from manufacturing to online empires. He’s seen it all—and he’s here to share what not to do when chasing growth. Spoiler: Buying three businesses in six months with zero integration strategy? That’s not scaling. That’s self-sabotage. In this no-fluff convo, you’ll learn: ✔️ The explosive difference between a strategic buyer and a chaotic cowboy ✔️ Why some acquisitions implode and drain value instead of adding it ✔️ How to prep your current business to absorb acquisitions without blowing it up ✔️ The secret to thinking beyond the buy—to integration and exit strategy ✔️ How to build a business so irresistible that even your competitors want to buy it If you’ve ever thought, “Maybe I’ll just buy another business and double my revenue,” you need to hear this. 🎧 Tune in now to learn how to grow through acquisition… without blowing up your business in the process.   Episode Highlights 06:30 – The importance of understanding the buyer’s mindset, especially when preparing to exit your business. 08:45 – Common reasons businesses fail to sell — including overvaluation, poor documentation, and lack of transferable leadership. 11:20 – Why “deal fever” can cloud entrepreneurs’ judgment and lead to bad acquisitions. 14:10 – Cultural fit and leadership alignment: often the real reasons integrations fail after a deal. 22:50 – Lessons learned from failed deals and red flags to look out for before signing. 26:30 – Strategic vs. opportunistic acquisitions — why clarity in intent is key. 28:45 – How to prepare your business for exit years in advance, including systemization and leadership planning.   Key Takeaways ➥ Being selective is critical—just because an opportunity arises doesn’t mean it’s the right fit for your business or your life. ➥ The buyer’s perspective matters—sellers must see their business through the lens of the acquirer: is it transferable? sustainable? well-documented? ➥ Leadership and culture are make-or-break factors in post-acquisition integration. Without the right leadership in place, the acquired business often struggles. ➥ Deal fever is real—don’t let excitement override discipline. Stick to your acquisition criteria and due diligence process. ➥ Exiting a business is a long game—the most successful exits come from those who plan years, building systems and leadership teams that can thrive without the founder. ➥ Avoiding mistakes means preparation, patience, and perspective—take your time, ask the right questions, and align your acquisitions with long-term strategy.   About Michael Vann Michael Vann is the President of The Vann Group, a family-owned firm that provides strategic consulting and transactional advisory services to privately held businesses. With over 25 years of experience, Michael helps owners scale, plan for succession, and maximize value. He’s also a principal at Eaton Square, a global investment banking firm, and a certified Predictable Success Scale Architect. Michael has advised on deals up to $50 million across industries like manufacturing, services, construction, and hospitality. He’s the co-author of Buying Out the Boss and the forthcoming High Performing Value, and frequently speaks on value building and business transitions. Michael lives in South Hadley, Massachusetts, with his wife, two daughters, and one unruly pup.   Connect with Michael Vann ➥https://www.linkedin.com/in/michaelvann/  ➥www.vann-group.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Exiting a business can be one of the most rewarding moments of an entrepreneur’s journey—or one of the most costly mistakes if handled poorly. Many sellers unknowingly leave hundreds of thousands, even millions of dollars, on the table simply because they aren’t prepared for the exit process. Jaryd Krause speaks with Domenic Rinaldi, a seasoned M&A advisor and owner of Sun Acquisitions, who has successfully guided over 500 business transactions. As the founder of K2 Advisor, Domenic specializes in helping business owners understand exactly what it takes to execute a profitable and stress-free exit. Together, they break down the biggest mistakes sellers make when exiting their businesses and how to avoid them.  You’ll discover: ✔️ How owner involvement and single-source dependencies can destroy your business valuation ✔️ Why many sellers are blindsided by market shifts, tariffs, and environmental changes ✔️ The critical role of value drivers and how to identify them before going to market ✔️ What can go catastrophically wrong during a deal—and how the right advisory team can prevent it ✔️ Why you should always be “exit ready,” even if selling isn’t on your immediate horizon If you’re preparing to sell your business—or simply want to protect the value you’ve built—this episode is packed with actionable insights to help you exit on top. 🎧 Listen now and learn how to exit your business the smart way. Episode Highlights 02:18 – Why most sellers leave money on the table when exiting their business 05:42 – How owner dependence and single-source revenue can destroy valuation 08:15 – Common risks in the current market, including tariffs and environmental changes 11:35 – Value drivers Domenic looks for when assessing a business for sale 14:50 – The importance of due diligence and how small oversights can become costly 17:30 – Why sellers must always be “exit-ready,” even if they’re not planning to sell soon 20:10 – Choosing the right advisory team: lawyers, accountants, and M&A experts who can make or break your exit Key Takeaways ➥ Seller mistakes are costly. Failing to prepare for an exit can result in leaving hundreds of thousands—or even millions—of dollars on the table. ➥ Owner dependency kills value. Businesses overly reliant on the owner, single customers, or single traffic sources are heavily discounted by buyers. ➥ Market conditions matter. External factors like tariffs, environmental shifts, or regulatory changes can impact valuation. Smart sellers plan for these contingencies in advance. ➥ Value drivers determine your sale price. Revenue diversity, strong cash flow, and documented systems all increase buyer confidence and the multiple you can command. ➥ Due diligence is non-negotiable. Small errors or overlooked liabilities can derail a deal. A proactive approach prevents last-minute surprises. ➥ Always be exit-ready. Even if you’re not planning to sell, setting up your business for a smooth exit ensures you’re prepared for unexpected life events or market opportunities. ➥ The right team is critical. Experienced lawyers, accountants, and M&A advisors can prevent deal disasters and protect your financial outcome.   About Domenic Rinaldi A seasoned M&A adviser, Domenic Rinaldi is the Owner and Managing Partner of the firm, Sun Acquisitions. He also founded K2Adviser to educate business owners on the requirements for a successful exit, acquisition, or scaling process.     Connect with Domenic Rinaldi ➥https://buyingonlinebusinesses.com/ep-087-why-you-need-seasoned-vets-on-your-team-when-buying-selling-businesses/ ➥www.sunacquisitions.com   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ GoDaddy (Website Hosting) - https://bit.ly/3YiRkWV ➥ Non Agency (SEO Audit) - https://bit.ly/3EPd7OZ ➥ Market Muse (Content Marketing Software) - https://bit.ly/3Me39L0   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Running a business is about building something that works without you, not just putting in the hours. But far too many entrepreneurs stay stuck in the weeds, overwhelmed by daily tasks and unclear on how to truly scale. That’s where systems—and now, AI—change everything. In this conversation, Jaryd Krause is joined by David Jenyns, founder of Systemology and author of SYSTEMology and The Systems Champion, to unpack how smart systems combined with the power of AI are transforming the way online businesses grow. David has built and sold multiple companies, helped hundreds of business owners systemize their operations, and now leads the conversation on how AI can be used not just to support teams, but to replace certain roles altogether. You’ll learn: ✔️ How to use AI to build and improve systems in your business✔️ Why experienced talent plus AI is replacing the traditional VA model✔️ How to step back from your business without losing momentum✔️ Real-life examples of AI replacing inefficiencies and boosting profits When it comes to growing your business, reclaiming your time, and creating something that endures, this episode is packed with useful strategies and steps to follow. 🎧 Tune in now and learn how to scale smarter with the systems + AI advantage.   Episode Highlights 01:44 – Why systemizing your business is critical for growth and freedom 06:15 – How to commit fully and overcome resistance when building systems 12:30 – The role and impact of a systems champion in scaling your business 19:30 – Where a systems champion fits in and how to identify the right person 22:00 – The transformative power of AI in systemizing processes and operations 27:30 – Real-life example of AI disrupting traditional business documentation 32:00 – How AI enhances the productivity of skilled team members and shrinks teams 35:00 – Using AI strategically to outperform competitors and grow faster   Key Takeaways ➥ Committing fully to systemizing your business culture is essential; half-measures lead to failure due to team resistance. ➥ Hiring a systems champion is critical—they drive the systemization process and embed a culture of repeatability and efficiency. ➥ Business owners need to shift focus from daily tasks to strategic growth, enabled by well-documented systems and strong teams. ➥ AI tools like ChatGPT and Google Gemini accelerate system documentation, process optimization, and strategic decision-making. ➥ AI adoption leads to smaller, more skilled teams who leverage technology to produce higher-quality results. ➥ Privacy concerns around AI data use require careful selection of secure platforms to protect business information. ➥ The systems champion role is evolving to include AI management, programming workflows, and ensuring the accuracy of AI outputs. ➥ Businesses embracing AI and systems now will stay competitive; those who resist risk falling behind in a rapidly changing landscape.   About David Jenyns David Jenyns is an experienced entrepreneur who sold the Melbourne Cricket Ground in his early twenties and founded Melbourne SEO Services. He systematized himself out of that business in 2016 and founded SYSTEMology to help business owners implement systems to scale their business. Today, he supports a growing community of certified SYSTEMologists, delivers workshops, keynote addresses hosts a podcast, and is on a mission to free business owners worldwide from daily operations.    Connect with David Jenyns ➥ https://www.systemology.com/scbook/ ➥ https://www.systemology.com/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Convert Kit  (Email Service Provider) - https://bit.ly/3o10Xgx   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Understanding the fine print that could make or break your deal is just as important when purchasing a business with SBA financing as it is when obtaining a loan. All too frequently, buyers lose out on opportunities or become mired in transactions that don't fit the program because they are unaware of the nuances of SBA regulations. The CEO of SBA Loan Group, Yankie Markowitz, sits down with Jaryd Krause in this episode to discuss his extensive knowledge of SBA loans and how he has facilitated more than $1 billion in SBA and real estate transactions. Yankie explains which business categories are eligible for SBA financing, what has changed recently, and how to handle the complex world of debt ratios, deal structures, and cash requirements. You’ll learn: ✔️ Which businesses can—and can’t—be acquired with SBA loans ✔️ How much cash do you need to qualify ✔️ Why e-commerce fits well with SBA financing, and where it falls short ✔️ The ins and outs of seller notes, holdbacks, and loan terms ✔️ Real-world lessons from deals that worked—and ones that didn’t This episode provides useful, straightforward advice from one of the most seasoned SBA specialists in the industry, regardless of whether you're prepared to purchase your first company or want to improve your acquisition approach. 🎧 To learn how to make SBA financing work for you and get closer to financial independence, listen now.   Episode Highlights 06:15 – Eligibility requirements and the role of creditworthiness in SBA loan approval 10:30 – Structuring deposits and how larger down payments can secure better interest rates 15:45 – Differences in loan terms and amortization for business vs. real estate purchases 20:20 – Prepayment penalties and their impact on SBA loan flexibility 23:00 – Utilizing seller notes and financing strategies in SBA deals 29:50 – Debt service coverage ratios and the importance of consistent cash flow Key Takeaways ➥ SBA financing is highly versatile, supporting working capital, inventory, real estate, and refinancing, but buyers must understand eligibility and lender-specific nuances. ➥ Seller financing (seller notes) can be incorporated into SBA deals but requires careful structuring to meet lender requirements and ensure adequate cash flow. ➥ Business valuation multiples generally range from 3-5x EBITDA for traditional businesses; higher multiples (like software businesses) often require substantially more equity upfront. ➥ Owning an existing profitable business simplifies acquiring complementary businesses by leveraging combined cash flow to support additional debt. ➥ Sustainable growth beats rapid expansion; business owners must carefully manage operational costs and cash flow to avoid overextension post-acquisition.   About Yankie Markowitz Yankie Markowitz is the Chief Executive Officer of SBA Loan Group. Yankie has helped facilitate over $1 billion dollars in SBA and real estate transactions, and complex deal syndication. He is often sought out by bankers to help structure intricate SBA transactions because of his knowledge and unique experience with the U.S. Small Business Administration loan programs.  Yankie is an Executive Board member for the Regional Business Assistance Corporation (an SBA CDC) and has been on the Loan Committee which allows him to work on hundreds of transactions for SBA each year. He also serves as a Board Member of Crown Heights Young Entrepreneur, a non-profit that is a full-service business resource center specifically tailored to fit the unique needs for aspiring entrepreneurs that focus on promoting responsible business development and providing them with the tools and resources that they need in order to achieve lifelong financial independence.    Connect with Yankie Markowitz ➥ https://sbaloangroup.com/ ➥https://finwise.podbean.com/e/finwise-eye-on-sba-lending-yankie-markowitz-ceo-sba-loan-group/   Resource Links ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s ➥ Rank Math (Wordpress SEO Plugin) - https://bit.ly/3Acyjf4 ➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Buying or selling a business isn’t just a transaction — it’s a turning point. But too often, what buyers think they want and what sellers believe they deserve don’t line up with reality. The result? Stalled deals, missed opportunities, and plenty of frustration on both sides. In this episode, Jaryd Krause sits down with Matt Frisca, owner of Transworld Business Advisors of La Grange and Tinley Park, to unpack the biggest reasons deals fail—and what it really takes to make them work. With 20+ business sales closed annually and 50+ active listings, Matt shares real-world insights from both sides of the table. You’ll learn: ✔️ Why sellers struggle to exit cleanly✔️ Common mistakes buyers make (and how to avoid them)✔️ The truth about SBA financing and “no money down” deals✔️ What due diligence really looks like in today’s market Whether you're buying, selling, or just curious, this episode delivers raw advice and actionable strategies from a dealmaker who knows the game. 🎧 Listen now and get the inside track on what actually moves the needle in business acquisitions.   Episode Highlights 12:40 – Importance of motivated sellers and avoiding lead oversaturation 15:45 – The three biggest reasons businesses fail to sell: lack of motivation, messy financials, and unrealistic pricing 19:30 – Recent SBA lending rule changes and fees 22:45 – Why “no money down” deals are unrealistic 24:40 – Risks of inexperienced buyers buying big businesses 28:10 – How to be an attractive, prepared buyer 33:15 – Balancing due diligence and trust to avoid “paralysis by analysis”   Key Takeaways ➥ Motivated sellers, clean financials, and realistic prices are crucial.➥ Content marketing is replacing paid ads due to cost hikes.➥ Seller equity rollovers now carry higher risk for sellers.➥ “No money down” deals rarely work; buyers need funds and experience.➥ Private equity adds competition for deals under $5M.➥ Prepared buyers with financing and clear plans succeed more.➥ Avoid overanalyzing—take calculated risks to close deals.   About Matt Frisca Matt Friscia runs and owns the Transworld Business Advisors of La Grange and Tinley Park with his team of 9 agents and one administrative assistant, focusing on main street and lower mid-market business brokerage. Their office handles over 20 successful closes a year, and they typically are working 50+ business for sale listings at any given time. Before joining Transworld, Matt worked in media sales for 15 years. Ten of those years were with the Disney company within their ESPN, ABC, and Radio Disney brands. He bought his first business, which was a franchise in the senior care field, back in 2016. He successfully grew that company and ultimately sold it five years later with Transworld Business Advisors.  His passion is helping small business owners with their business exit transactions while helping to super serve the underserved community of small businesses. Besides having played music professionally for the past 28 years, he enjoys watching his two children play sports, traveling and learning languages.   Connect with Matt Frisca ➥ https://www.tworld.com/    Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Convert Kit (Email Software Provider) - https://bit.ly/3o10Xgx   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Let’s be real — buying or selling a business is one of the biggest decisions you’ll ever make. Get it right, and it could be life-changing. Get it wrong… and the fallout could be brutal. That’s exactly why this week’s episode is a must-listen. Jaryd Krause sits down with Katarina Strandberg, a powerhouse Swedish business lawyer with deep expertise in venture capital, scale-ups, and M&A. She’s worked with founders, investors, and SME leaders across Europe, and brings not only legal chops but also perspective as an angel investor, published author, and university lecturer. Katarina has seen it all — and she’s here to share the real stories, the hard truths, and the clever strategies that can make or break your deal. In this episode, you’ll learn: ✔️ The biggest risks buyers face (and how to avoid stepping on legal landmines)✔️ What really happens during legal due diligence — and why it’s more than just paperwork✔️ How to deal with “deal fatigue” and who should keep cool when emotions run high✔️ Jaw-dropping stories of deals gone wrong — and the legal moves that could’ve saved them✔️ Clever deal structures and funding options that most people never think about✔️ How to avoid surprise legal bills (yes, it’s possible!)✔️ Why skipping legal help might be the most expensive mistake you ever make If you’ve ever felt overwhelmed by contracts, confused by due diligence, or just unsure about when to bring a lawyer in, this episode is your roadmap. 🎧 Tune in now and learn how to protect yourself, your deal, and your financial future — with smart legal strategy by your side.     Episode Highlights 02:50 – Why defining “online” vs “physical” businesses is crucial for strategy and contracts 07:10 – Ignoring a “change of control” clause led one buyer to lose supplier exclusivity overnight 08:15 – How proper due diligence helps uncover risks, negotiate price, and add protections 16:50 – Why non-compete agreements are critical to prevent the seller from becoming your competitor 21:40 – Managing emotions, trust, and “deal fatigue” is key to getting deals across the line 25:45 – Fixed legal fees and clear timelines reduce stress and prevent buyer fatigue 28:20 – Preparing buyers early for delays and emotional hurdles ensures smoother transactions   Key Takeaways ➥ Overlooking contract clauses (like change of control) can destroy business value overnight ➥ Buyers must normalize financials to reflect realistic salaries, working capital, and operational needs ➥ Strong non-compete agreements are non-negotiable to protect your investment ➥ Managing trust and emotions during diligence is just as important as the numbers ➥ Fixed-fee legal services and clear expectations help avoid surprises and fatigue ➥ Every deal involves risk — great advisors help you identify, price, and mitigate those risks effectively   About Katarina Strandberg Katarina Strandberg is a Swedish business lawyer specializing in venture capital, scale-ups, and M&A. She advises SME leaders and investors, drawing on her experience in deal structuring, fund law, and legislative work. A published author and angel investor, she’s also taught at Swedish universities and served on international advisory boards.   Connect with Katarina Strandberg ➥ https://www.youtube.com/@Businesslawtoolbox ➥https://www.stgcommerciallaw.com/    Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH   🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR     *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.

Strap in for a brutally honest conversation as Jaryd Krause sits down with none other than Elliot Holland,  a Harvard Business School alum, seasoned entrepreneur, and strategic founder. Elliot runs a seven-figure due diligence firm that performs "mini audits" on businesses, helping investors avoid being misled by clever sellers and slick brokers. With nearly 20 years of experience in small business acquisitions, Elliot has seen it all—and then some. From hidden red flags in financials to smoke-and-mirrors marketing metrics on Amazon and SEO-driven sites, he shares exactly where buyers get it wrong—and how those mistakes can cost you hundreds of thousands, or worse, your entire investment. This episode will pull back the curtain on how unsuspecting buyers get swindled into buying dud deals, all because they skipped real due diligence. Highlight the critical considerations buyers often miss in the acquisition process: ✔️ The most common (and costly) mistakes buyers make in due diligence✔️ Why relationships with sellers matter—and how they can go sideways fast✔️ How sellers can mislead or manipulate the narrative to close a deal✔️ Financial vs. marketing due diligence—what most acquirers overlook✔️ The frameworks Elliot uses to assess businesses like an expert This is not just theory—Elliot has personally helped countless clients dodge bad deals and secure multi-million-dollar wins, all by demystifying the due diligence process. With his signature humor, straight talk, and lived experience, he makes complex business buying principles not only clear but actionable. Whether you're a first-time acquirer or scaling your portfolio, this episode will save you more than money—it could save your sanity. Don’t even think about buying a business until you listen to this conversation.    Episode Highlights 04:15 – Red flags usually show as many small issues rather than one big problem 10:30 – Verifying seller’s time commitment by reviewing task lists and holding strategy meetings 18:45 – Wanting shortcuts in due diligence can lead to costly mistakes 23:00 – Sellers often resist reasonable buyer requests like strong non-competes and management interviews 26:10 – Negotiation is a strategic dance where sellers test buyer strength 29:15 – Cheaper advisors often bring higher risks and lower value on seven-figure deals   Key Takeaways ➥ Red flags are subtle and require a sharp, skeptical mindset to detect ➥ Sellers use stories and distractions instead of admitting flaws outright ➥ Due diligence takes time and can be uncomfortable but shortcuts are costly ➥ Experienced advisors are critical for high-value deals to avoid disaster ➥ Buyers need to be ready to walk away if sellers are not transparent or cooperative ➥ Emotional detachment helps buyers make better decisions and negotiate smarter   About Elliot Holland Elliott Holland is a Harvard Business School alum, former business acquirer & OG in small business acquisitions.  He runs TheBusinessBuyingMasterclass.com and a 7-figure business that does "mini audits" on businesses before clients acquire them to be sure they're not swindled.  With nearly two decades of experience, Elliott empowers everyday investors to acquire million-dollar businesses because he's been in their shoes and offers insight others cannot.   Elliott simplifies complex small business buying concepts with humor so that everyday investors can understand.   With over 100 podcast appearances and speaking engagements at top business schools, Elliott shares expertise on entrepreneurship, investing, and business buying.   Connect with Elliot Holland ➥ https://www.linkedin.com/in/elliottholland/   Resource Links ➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com ➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/ ➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/ ➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/ ➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause ➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u ➥ Link Whisper (SEO tool for internal linking on websites) - https://bit.ly/3l7K7Ld ➥ Active Campaign (Email Software Provider) - https://bit.ly/3DCwYQH 🔥Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥 ➥ Empire Flippers - https://bit.ly/3RtyMkE ➥ Flippa - https://bit.ly/3wGa8r5 ➥ Motion Invest - https://bit.ly/3YmJAmO ➥ Investors Club - https://bit.ly/3ZpgioR   *This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.See omnystudio.com/listener for privacy information.